neal054

Table 1 Crystal data and structure refinement for neal054.
Identification code	neal054
Empirical formula	C₁₇H₂₃N₂O₄I
Formula weight	446.27
Temperature/K	100.0
Crystal system	monoclinic
Space group	P2₁
a/Å	6.2572(5)
b/Å	11.7630(9)
c/Å	13.0387(10)
α/°	90
β/°	96.657(3)
γ/°	90
Volume/Å³	953.22(13)
Z	2
ρ_calcg/cm³	1.555
μ/mm^‑1	13.387
F(000)	448.0
Crystal size/mm³	0.172 × 0.099 × 0.028
Radiation	CuKα (λ = 1.54178)
2Θ range for data collection/°	6.826 to 127.624
Index ranges	-7 ≤ h ≤ 7, -13 ≤ k ≤ 13, -15 ≤ l ≤ 15
Reflections collected	18078
Independent reflections	3118 [R_int = 0.0562, R_sigma = 0.0339]
Data/restraints/parameters	3118/1/265
Goodness-of-fit on F²	1.077
Final R indexes [I>=2σ (I)]	R₁ = 0.0325, wR₂ = 0.0868
Final R indexes [all data]	R₁ = 0.0330, wR₂ = 0.0873
Largest diff. peak/hole / e Å^-3	0.87/-0.47
Flack parameter	-0.024(6)

Table 2 Fractional Atomic Coordinates (×10⁴) and Equivalent Isotropic Displacement Parameters (Å²×10³) for neal054. U_eq is defined as 1/3 of of the trace of the orthogonalised U_IJ tensor.
Atom	x	y	z	U(eq)
I1	10714.0(7)	2081.0(4)	-295.7(3)	42.93(19)
O1	-42(8)	5895(4)	4382(4)	34.6(11)
O2	4422(7)	5932(4)	6055(3)	23.9(9)
O3	5956(7)	4270(4)	5616(3)	23.0(9)
O4	4810(8)	5501(4)	1694(4)	32.1(11)
N1	794(10)	7701(6)	4885(5)	25.1(14)
N2	4497(8)	5523(4)	4410(4)	20.1(11)
C1	-1245(12)	7957(7)	5262(7)	39.5(18)
C2	1220(11)	6695(5)	4487(6)	22.1(13)
C3	3465(10)	6617(5)	4132(5)	20.7(13)
C4	3388(13)	6631(7)	2956(6)	28.1(15)
C5	5233(11)	5883(6)	2735(5)	25.9(13)
C6	5244(11)	4943(5)	3535(5)	22.2(13)
C7	5035(10)	5167(5)	5385(5)	19.7(13)
C8	4522(12)	5649(6)	7166(5)	30.9(15)
C9	6833(14)	5461(7)	7629(6)	39.6(18)
C10	3082(14)	4621(7)	7296(6)	40.4(19)
C11	3569(17)	6704(7)	7591(7)	52(2)
C12	5482(13)	4248(7)	389(6)	35.2(16)
C13	6763(13)	3497(7)	-64(6)	36.7(17)
C14	8843(12)	3291(6)	382(5)	32.4(16)
C15	9642(12)	3828(6)	1297(5)	28.6(14)
C16	8325(12)	4566(6)	1764(6)	30.2(15)
C17	6258(11)	4785(6)	1321(5)	29.6(14)

Table 2 Fractional Atomic Coordinates (×10⁴) and Equivalent Isotropic Displacement Parameters (Å²×10³) for neal054. U_eq is defined as 1/3 of of the trace of the orthogonalised U_IJ tensor.

Atom

U(eq)

10714.0(7)

2081.0(4)

-295.7(3)

42.93(19)

-42(8)

5895(4)

4382(4)

34.6(11)

4422(7)

5932(4)

6055(3)

23.9(9)

5956(7)

4270(4)

5616(3)

23.0(9)

4810(8)

5501(4)

1694(4)

32.1(11)

794(10)

7701(6)

4885(5)

25.1(14)

4497(8)

5523(4)

4410(4)

20.1(11)

-1245(12)

7957(7)

5262(7)

39.5(18)

1220(11)

6695(5)

4487(6)

22.1(13)

3465(10)

6617(5)

4132(5)

20.7(13)

3388(13)

6631(7)

2956(6)

28.1(15)

5233(11)

5883(6)

2735(5)

25.9(13)

5244(11)

4943(5)

3535(5)

22.2(13)

5035(10)

5167(5)

5385(5)

19.7(13)

4522(12)

5649(6)

7166(5)

30.9(15)

6833(14)

5461(7)

7629(6)

39.6(18)

C10

3082(14)

4621(7)

7296(6)

40.4(19)

C11

3569(17)

6704(7)

7591(7)

52(2)

C12

5482(13)

4248(7)

389(6)

35.2(16)

C13

6763(13)

3497(7)

-64(6)

36.7(17)

C14

8843(12)

3291(6)

382(5)

32.4(16)

C15

9642(12)

3828(6)

1297(5)

28.6(14)

C16

8325(12)

4566(6)

1764(6)

30.2(15)

C17

6258(11)

4785(6)

1321(5)

29.6(14)

Table 3 Anisotropic Displacement Parameters (Å²×10³) for neal054. The Anisotropic displacement factor exponent takes the form: -2π²[h²a*²U₁₁+2hka*b*U₁₂+…].
Atom	U₁₁	U₂₂	U₃₃	U₂₃	U₁₃	U₁₂
I1	50.3(3)	47.3(3)	30.0(3)	-11.2(2)	-0.10(17)	9.7(3)
O1	26(2)	26(2)	51(3)	-4(2)	3(2)	-3(2)
O2	33(2)	19(2)	20(2)	-3.2(17)	4.5(18)	7.1(18)
O3	28(2)	15(2)	27(2)	-0.4(17)	7.6(18)	4.4(18)
O4	34(3)	42(3)	20(2)	-2(2)	2.1(19)	2(2)
N1	20(3)	18(3)	38(4)	-1(3)	6(3)	-1(2)
N2	23(3)	16(3)	22(3)	-3(2)	4(2)	2(2)
C1	27(3)	28(4)	65(6)	2(3)	12(3)	2(3)
C2	17(3)	16(3)	32(3)	5(3)	-1(3)	-3(2)
C3	20(3)	18(3)	24(3)	0(2)	-1(3)	1(2)
C4	35(4)	21(3)	27(4)	4(3)	-1(3)	-1(3)
C5	29(3)	31(3)	18(3)	1(3)	3(3)	-6(3)
C6	27(3)	21(3)	21(3)	-2(2)	8(3)	-5(3)
C7	18(3)	16(3)	25(3)	-5(2)	4(2)	-3(2)
C8	44(4)	31(4)	19(3)	-4(3)	8(3)	4(3)
C9	49(5)	42(4)	25(4)	1(3)	-5(3)	-1(4)
C10	47(4)	43(4)	35(4)	8(3)	24(4)	3(4)
C11	81(6)	43(5)	34(4)	-10(3)	21(4)	16(4)
C12	40(4)	44(4)	21(4)	2(3)	0(3)	-3(3)
C13	43(4)	49(5)	17(4)	-5(3)	0(3)	-2(3)
C14	43(4)	31(4)	25(4)	-3(3)	11(3)	4(3)
C15	30(4)	32(4)	24(3)	1(3)	2(3)	-5(3)
C16	36(4)	34(4)	22(3)	-1(3)	7(3)	-8(3)
C17	32(3)	37(4)	21(3)	3(3)	7(3)	-9(3)

Table 3 Anisotropic Displacement Parameters (Å²×10³) for neal054. The Anisotropic displacement factor exponent takes the form: -2π²[h²a*²U₁₁+2hka*b*U₁₂+…].

Atom

U₁₁

U₂₂

U₃₃

U₂₃

U₁₃

U₁₂

50.3(3)

47.3(3)

30.0(3)

-11.2(2)

-0.10(17)

9.7(3)

26(2)

51(3)

-4(2)

3(2)

-3(2)

33(2)

19(2)

20(2)

-3.2(17)

4.5(18)

7.1(18)

28(2)

15(2)

27(2)

-0.4(17)

7.6(18)

4.4(18)

34(3)

42(3)

20(2)

-2(2)

2.1(19)

2(2)

20(3)

18(3)

38(4)

-1(3)

6(3)

-1(2)

23(3)

16(3)

22(3)

-3(2)

4(2)

2(2)

27(3)

28(4)

65(6)

2(3)

12(3)

2(3)

17(3)

16(3)

32(3)

5(3)

-1(3)

-3(2)

20(3)

18(3)

24(3)

0(2)

-1(3)

1(2)

35(4)

21(3)

27(4)

4(3)

-1(3)

29(3)

31(3)

18(3)

1(3)

3(3)

-6(3)

27(3)

21(3)

-2(2)

8(3)

-5(3)

18(3)

16(3)

25(3)

-5(2)

4(2)

-3(2)

44(4)

31(4)

19(3)

-4(3)

8(3)

4(3)

49(5)

42(4)

25(4)

1(3)

-5(3)

-1(4)

C10

47(4)

43(4)

35(4)

8(3)

24(4)

3(4)

C11

81(6)

43(5)

34(4)

-10(3)

21(4)

16(4)

C12

40(4)

44(4)

21(4)

2(3)

0(3)

-3(3)

C13

43(4)

49(5)

17(4)

-5(3)

0(3)

-2(3)

C14

43(4)

31(4)

25(4)

-3(3)

11(3)

4(3)

C15

30(4)

32(4)

24(3)

1(3)

2(3)

-5(3)

C16

36(4)

34(4)

22(3)

-1(3)

7(3)

-8(3)

C17

32(3)

37(4)

21(3)

3(3)

7(3)

-9(3)

Table 4 Bond Lengths for neal054.
Atom	Atom	Length/Å	Atom	Atom	Length/Å
I1	C14	2.101(7)	C3	C4	1.529(10)
O1	C2	1.225(8)	C4	C5	1.506(10)
O2	C7	1.341(7)	C5	C6	1.520(9)
O2	C8	1.481(8)	C8	C9	1.517(11)
O3	C7	1.223(8)	C8	C10	1.528(11)
O4	C5	1.425(8)	C8	C11	1.510(10)
O4	C17	1.367(9)	C12	C13	1.371(12)
N1	C1	1.451(9)	C12	C17	1.405(11)
N1	C2	1.331(9)	C13	C14	1.384(11)
N2	C3	1.466(8)	C14	C15	1.390(10)
N2	C6	1.452(8)	C15	C16	1.386(11)
N2	C7	1.344(9)	C16	C17	1.378(11)
C2	C3	1.532(9)

Table 4 Bond Lengths for neal054.

Atom

Length/Å

Atom

Length/Å

C14

2.101(7)

1.529(10)

1.225(8)

1.506(10)

1.341(7)

1.520(9)

1.481(8)

1.517(11)

1.223(8)

C10

1.528(11)

1.425(8)

C11

1.510(10)

C17

1.367(9)

C12

C13

1.371(12)

1.451(9)

C12

C17

1.405(11)

1.331(9)

C13

C14

1.384(11)

1.466(8)

C14

C15

1.390(10)

1.452(8)

C15

C16

1.386(11)

1.344(9)

C16

C17

1.378(11)

1.532(9)

Table 5 Bond Angles for neal054.
Atom	Atom	Atom	Angle/˚	Atom	Atom	Atom	Angle/˚
C7	O2	C8	120.2(5)	O3	C7	O2	125.5(6)
C17	O4	C5	118.4(5)	O3	C7	N2	124.1(5)
C2	N1	C1	122.7(7)	O2	C8	C9	110.6(6)
C6	N2	C3	113.0(5)	O2	C8	C10	109.1(6)
C7	N2	C3	124.2(5)	O2	C8	C11	101.5(6)
C7	N2	C6	121.9(5)	C9	C8	C10	112.8(7)
O1	C2	N1	124.8(7)	C11	C8	C9	111.9(7)
O1	C2	C3	121.4(6)	C11	C8	C10	110.3(7)
N1	C2	C3	113.8(6)	C13	C12	C17	120.1(7)
N2	C3	C2	111.8(5)	C12	C13	C14	120.0(7)
N2	C3	C4	102.7(5)	C13	C14	I1	119.0(5)
C4	C3	C2	112.3(6)	C13	C14	C15	120.5(7)
C5	C4	C3	104.5(6)	C15	C14	I1	120.4(6)
O4	C5	C4	107.7(6)	C16	C15	C14	119.3(7)
O4	C5	C6	114.2(5)	C17	C16	C15	120.6(7)
C4	C5	C6	103.7(5)	O4	C17	C12	114.1(7)
N2	C6	C5	102.8(5)	O4	C17	C16	126.4(7)
O2	C7	N2	110.4(5)	C16	C17	C12	119.5(7)

Table 5 Bond Angles for neal054.

Atom

Angle/˚

Atom

Angle/˚

120.2(5)

125.5(6)

C17

118.4(5)

124.1(5)

122.7(7)

110.6(6)

113.0(5)

C10

109.1(6)

124.2(5)

C11

101.5(6)

121.9(5)

C10

112.8(7)

124.8(7)

C11

111.9(7)

121.4(6)

C11

C10

110.3(7)

113.8(6)

C13

C12

C17

120.1(7)

111.8(5)

C12

C13

C14

120.0(7)

102.7(5)

C13

C14

119.0(5)

112.3(6)

C13

C14

C15

120.5(7)

104.5(6)

C15

C14

120.4(6)

107.7(6)

C16

C15

C14

119.3(7)

114.2(5)

C17

C16

C15

120.6(7)

103.7(5)

C17

C12

114.1(7)

102.8(5)

C17

C16

126.4(7)

110.4(5)

C16

C17

C12

119.5(7)

Table 6 Torsion Angles for neal054.
A	B	C	D	Angle/˚	A	B	C	D	Angle/˚
I1	C14	C15	C16	-175.8(5)	C6	N2	C7	O3	-9.1(9)
O1	C2	C3	N2	-43.0(9)	C7	O2	C8	C9	64.6(8)
O1	C2	C3	C4	71.8(8)	C7	O2	C8	C10	-60.1(8)
O4	C5	C6	N2	-149.2(5)	C7	O2	C8	C11	-176.5(6)
N1	C2	C3	N2	138.5(6)	C7	N2	C3	C2	-63.9(8)
N1	C2	C3	C4	-106.7(7)	C7	N2	C3	C4	175.6(6)
N2	C3	C4	C5	-26.5(7)	C7	N2	C6	C5	-153.4(6)
C1	N1	C2	O1	1.1(11)	C8	O2	C7	O3	-10.0(9)
C1	N1	C2	C3	179.6(7)	C8	O2	C7	N2	170.1(5)
C2	C3	C4	C5	-146.7(6)	C12	C13	C14	I1	177.3(6)
C3	N2	C6	C5	16.3(7)	C12	C13	C14	C15	0.8(12)
C3	N2	C7	O2	2.3(8)	C13	C12	C17	O4	-179.3(7)
C3	N2	C7	O3	-177.6(6)	C13	C12	C17	C16	1.1(11)
C3	C4	C5	O4	158.2(5)	C13	C14	C15	C16	0.6(11)
C3	C4	C5	C6	36.9(7)	C14	C15	C16	C17	-1.2(10)
C4	C5	C6	N2	-32.3(7)	C15	C16	C17	O4	-179.2(6)
C5	O4	C17	C12	165.9(6)	C15	C16	C17	C12	0.3(10)
C5	O4	C17	C16	-14.6(10)	C17	O4	C5	C4	-178.7(6)
C6	N2	C3	C2	126.7(6)	C17	O4	C5	C6	-64.2(7)
C6	N2	C3	C4	6.1(7)	C17	C12	C13	C14	-1.7(12)
C6	N2	C7	O2	170.8(5)

Table 6 Torsion Angles for neal054.

Angle/˚

C14

C15

C16

-175.8(5)

-9.1(9)

-43.0(9)

64.6(8)

71.8(8)

C10

-60.1(8)

-149.2(5)

C11

-176.5(6)

138.5(6)

-63.9(8)

-106.7(7)

175.6(6)

-26.5(7)

-153.4(6)

1.1(11)

-10.0(9)

179.6(7)

170.1(5)

-146.7(6)

C12

C13

C14

177.3(6)

16.3(7)

C12

C13

C14

C15

0.8(12)

2.3(8)

C13

C12

C17

-179.3(7)

-177.6(6)

C13

C12

C17

C16

1.1(11)

158.2(5)

C13

C14

C15

C16

0.6(11)

36.9(7)

C14

C15

C16

C17

-1.2(10)

-32.3(7)

C15

C16

C17

-179.2(6)

C17

C12

165.9(6)

C15

C16

C17

C12

0.3(10)

C17

C16

-14.6(10)

C17

-178.7(6)

126.7(6)

C17

-64.2(7)

6.1(7)

C17

C12

C13

C14

-1.7(12)

170.8(5)

Table 7 Hydrogen Atom Coordinates (Å×10⁴) and Isotropic Displacement Parameters (Å²×10³) for neal054.
Atom	x	y	z	U(eq)
H1	1490(130)	8150(70)	4880(60)	10(20)
H1A	-1162.58	8705.78	5594.76	59
H1B	-1557.73	7378.32	5764.49	59
H1C	-2391.77	7961.06	4682.71	59
H3	4310(90)	7280(60)	4410(50)	11(15)
H4A	3410(110)	7340(70)	2700(50)	15(17)
H4B	2200(130)	6230(70)	2770(60)	23(18)
H5	6550(140)	6370(70)	2800(70)	40(20)
H6A	4090(120)	4350(70)	3260(60)	29(19)
H6B	6710(170)	4670(80)	3680(80)	50(30)
H9A	7374.19	4753.49	7358.31	59
H9B	6895.3	5409.49	8382.42	59
H9C	7721.52	6099.37	7446.55	59
H10A	1690.9	4729.7	6878.56	61
H10B	2860.2	4542.85	8024.06	61
H10C	3772.85	3933.25	7067.49	61
H11A	4430.61	7367.3	7444.07	77
H11B	3567.73	6625.28	8339.01	77
H11C	2089.16	6803.79	7264.89	77
H12	3960(190)	4360(120)	200(90)	70(40)
H13	6220(120)	3130(70)	-580(70)	23(18)
H15	10900(130)	3660(70)	1610(60)	25(19)
H16	8770(120)	4970(70)	2350(70)	30(20)

Table 7 Hydrogen Atom Coordinates (Å×10⁴) and Isotropic Displacement Parameters (Å²×10³) for neal054.

Atom

U(eq)

1490(130)

8150(70)

4880(60)

10(20)

H1A

-1162.58

8705.78

5594.76

H1B

-1557.73

7378.32

5764.49

H1C

-2391.77

7961.06

4682.71

4310(90)

7280(60)

4410(50)

11(15)

H4A

3410(110)

7340(70)

2700(50)

15(17)

H4B

2200(130)

6230(70)

2770(60)

23(18)

6550(140)

6370(70)

2800(70)

40(20)

H6A

4090(120)

4350(70)

3260(60)

29(19)

H6B

6710(170)

4670(80)

3680(80)

50(30)

H9A

7374.19

4753.49

7358.31

H9B

6895.3

5409.49

8382.42

H9C

7721.52

6099.37

7446.55

H10A

1690.9

4729.7

6878.56

H10B

2860.2

4542.85

8024.06

H10C

3772.85

3933.25

7067.49

H11A

4430.61

7367.3

7444.07

H11B

3567.73

6625.28

8339.01

H11C

2089.16

6803.79

7264.89

H12

3960(190)

4360(120)

200(90)

70(40)

H13

6220(120)

3130(70)

-580(70)

23(18)

H15

10900(130)

3660(70)

1610(60)

25(19)

H16

8770(120)

4970(70)

2350(70)

30(20)

Experimental

Single crystals of C₁₇H₂₃N₂O₄I [neal054] were []. A suitable crystal was selected and [mounted with perfluoroalkane oil on plastic loop] on a Bruker Venture Photon III diffractometer. The crystal was kept at 100.0 K during data collection. Using Olex2 [1], the structure was solved with the SHELXT [2] structure solution program using Intrinsic Phasing and refined with the XL [3] refinement package using Least Squares minimisation.

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341.
Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Crystal structure determination of [neal054]

Crystal Data for C₁₇H₂₃N₂O₄I (M =446.27 g/mol): monoclinic, space group P2₁ (no. 4), a = 6.2572(5) Å, b = 11.7630(9) Å, c = 13.0387(10) Å, β = 96.657(3)°, V = 953.22(13) Å³, Z = 2, T = 100.0 K, μ(CuKα) = 13.387 mm^-1, Dcalc = 1.555 g/cm³, 18078 reflections measured (6.826° ≤ 2Θ ≤ 127.624°), 3118 unique (R_int = 0.0562, R_sigma = 0.0339) which were used in all calculations. The final R₁ was 0.0325 (I > 2σ(I)) and wR₂ was 0.0873 (all data).

Refinement model description

Number of restraints - 1, number of constraints - unknown.

Details:

1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)

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